Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G6/00—Condensation polymers of aldehydes or ketones only
  • C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones

Definitions

• the invention relates to ketone-aldehyde resins with very broad solubility properties and low color numbers, a process for their preparation and their use as Main component, base component or additional component in coating agents, Printing inks, pigment and tinting pastes, ballpoint pen pastes, inks, polishes, adhesives and sealants and insulation materials.
• the object of the present invention was to provide resins with low intrinsic color and at the same time Broad solubility in a wide variety of solvents and broad compatibility with others To produce paint raw materials.
• EP 0 668 301 describes the preparation of ketone-aldehyde resins. After there The processes described have such products with relatively high color numbers. The usage phase transfer catalysts in particular are not described.
• EP 0 007 106 describes polycondensation products from aliphatic and cyclic Ketones, which, produced by the process disclosed there, have very high softening ranges and therefore have comparatively high molecular weights.
• the resins are not soluble in aliphatic solvents.
• the phase transfer catalysts used there have no aromatic residues.
• the ketone-aldehyde resins according to the invention are in practically all for coatings in Question organic solvents, especially mineral oils, mineral spirits and Aliphatic, soluble. They are also soluble in alcoholic solvents such as ethanol. So that is given the possibility of low-odor, environmentally friendly and toxicologically harmless Formulate coating materials.
• the ketone-aldehyde resins according to the invention are widely compatible with Binders and resins. They are especially like with relatively non-polar types Long oil alkyd resins, natural oils, hydrocarbon resins can also be mixed polar types such as Polyesters, polyamides, polyacrylates, nitrocellulose, etc.
• Stable pigment preparations can be made from the ketone-aldehyde resins according to the invention and formulate tinting pastes due to their broad compatibility in most Coating materials can be used and have excellent coloristic properties to lead.
• the resins relevant to the invention can Increase the solids content of such products so that the proportion of organic solvents can be reduced.
• the ketone-aldehyde resins according to the invention can be cyclohexanone and all alkyl-substituted Cyclohexanones with one or more alkyl radicals, the total of 1 to 8 Have hydrocarbon atoms, contained individually or in a mixture.
• you can 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone.
• Cyclohexanone, 4-tert-butylcyclohexanone and 3,3,5-trimethylcyclohexanone are preferred.
• Suitable aliphatic aldehydes are in principle undisclosed or branched aldehydes, such as e.g. Formaldehyde, acetaldehyde, n-butyraldehyde and / or isobutyraldehyde and dodecanal etc.; however, formaldehyde is preferably used alone or in mixtures.
• the formaldehyde required is usually in the form of an approximately 25 to 40% strength by weight aqueous solution used.
• Other forms of use of formaldehyde such as also the use as paraformaldehyde or trioxane are also possible.
• Aromatic aldehydes, e.g. Benzaldehyde can also be contained in a mixture with formaldehyde.
• the ketone-aldehyde resins according to the invention can primarily be ketones, alone or in a mixture, contain the aliphatic, cycloaliphatic, aromatic or have mixed character. Examples include acetone, acetophenone, methyl ethyl ketone, Heptanone-2, Pentanone-3, methyl isobutyl ketone, cyclopentanone, cyclododecanone, mixtures from 2,2,4- and 2,4,4-trimethylcyclopentanone, cycloheptanone and cyclooctanone. However, methyl ethyl ketone and acetophenone are preferred. In general, everyone in the Literature for ketone resin syntheses as suitable ketones, usually all C-H-acidic Ketones.
• a particular embodiment of the invention includes mixtures of cyclohexanones.
• Mixtures of trimethylcyclohexanone / cyclohexanone are of particular importance in terms of application technology, 4-tert-butylcyclohexanone / trimethylcyclohexanone / cyclohexanone and 4-tert-butylcyclohexanone / trimethylcyclohexanone in molar mixing ratios of substituted cyclohexanones to the unsubstituted cyclohexanone from 0.1 to 0.9 to 0.9 to 0.1, preferably from 0.2 to 0.8 to 0.8 to 0.2, particularly preferably from 0.3 to 0.7 to 0.7 to 0.3 to.
• the ratio between the ketone component and the aldehyde component can vary between 1 to 0.9 to 1 to 4. However, a ketone / aldehyde ratio of 1 to 1 is preferred up to 1 to 2.
• alkyl radicals (R 2-4 ) with 1 to 22 C atoms, in particular those with 1 to 12 C atoms, in the carbon chain and / or phenyl and / or benzyl radicals and / or mixtures of the two are preferred .
• Benzyltributylammonium chloride is preferably used.
• R 2-4 alkyl radicals having 1 to 22 carbon atoms and / or phenyl radicals and / or benzyl radicals are preferred.
• quaternary ammonium salts are cetyldimethylbenzylammonium chloride, tributylbenzylammonium chloride, Trimethylbenzylammonium chloride, trimethylbenzylamminium iodide, Triethylbenzylammonium chloride or triethylbenzylammonium iodide.
• quaternary phosphonium salts come e.g. Triphenylbenzylphosphonium chloride or Triphenylbenzylphosphonium iodide in question. Mixtures can, however, also be used become.
• phase transfer catalyst according to the invention is used in amounts of 0.01 to 15 preferably from 0.1 to 10.0, and in particular in amounts from 0.1 to 5.0% by mass - Based on the ketone used - used in the polycondensation mixture.
• phase transfer catalyst In addition to the phase transfer catalyst, strongly basic compounds such as Alkali hydroxides, especially NaOH and / or KOH as catalysts for the Polycondensation used.
• strongly basic compounds such as Alkali hydroxides, especially NaOH and / or KOH as catalysts for the Polycondensation used.
• the basic catalysts are used in amounts of> 0.1 mol%, preferably> 1 mol% and especially in amounts of> 5 mol% - based on the ketone - in the Reaction mixture used.
• the resins of the invention are completely and clearly soluble as a 10 and 50% solution of ethanol and white spirit.
• the molar amounts used and the properties of the resins obtained are shown in the table remove. In this mode of operation, color numbers around 4 are common. The further analysis values of the Resins obtained serve as target parameters.

Landscapes

• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Phenolic Resins Or Amino Resins (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=33185794

Family Applications (1)

Country Status (9)

Cited By (1)

Families Citing this family (21)

Citations (4)

Family Cites Families (24)

• 2003
  • 2003-06-14 DE DE10326893A patent/DE10326893A1/de not_active Withdrawn
• 2004
  • 2004-04-21 EP EP04101655A patent/EP1486520A1/de not_active Withdrawn
  • 2004-06-08 TW TW093116465A patent/TW200502275A/zh unknown
  • 2004-06-09 BR BR0401930-0A patent/BRPI0401930A/pt not_active IP Right Cessation
  • 2004-06-09 US US10/863,369 patent/US20050010016A1/en not_active Abandoned
  • 2004-06-10 AU AU2004202618A patent/AU2004202618A1/en not_active Abandoned
  • 2004-06-11 CA CA002471189A patent/CA2471189A1/en not_active Abandoned
  • 2004-06-11 CN CN200410049037.XA patent/CN1315900C/zh not_active Expired - Fee Related
  • 2004-06-11 NO NO20042430A patent/NO20042430L/no not_active Application Discontinuation
• 2008
  • 2008-12-23 US US12/342,612 patent/US7812109B2/en not_active Expired - Fee Related

Patent Citations (5)

Also Published As

Similar Documents

Legal Events